When it comes to doing business, Jay-Z seems to have been graced with the Midas touch. The rapper has been involved in numerous lucrative business deals, and was recently placed at number one on Forbes’ “Top Earning Couples” list with wife and singer Beyonce.

On Thursday, however, Jay filed a $3.7 million lawsuit against investment firm Highland Capital Management over a 2007 loan for a hotel that was never opened. During that time, Hov reportedly borrowed $52 million to open his own hotel in Manhattan, to be christened the J Hotel. In order to avoid repossession, however, the rapper was forced to sell the loan to Highland when the property value fell due to an uncertain economy.

Jay-Z’s lawsuit claims that Highland’s unresponsiveness and consistent delay of negotiations regarding the loan led to a loss of $20,000 a day. According to the lawsuit, “This action arises out of the efforts by defendants [Highland Capital Management] to bleed additional funds from the plaintiff [Jay-Z].”

In response to the claim, the investment firm offered its own response. It said in a statement, “Highland believes the claims asserted by Mr. Carter are meritless, and [the company] will vigorously defend itself and intends to pursue the obligations owed to Highland’s investors by the borrower, Mr. Carter and the other guarantors.”

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No word yet on when the trial will happen.